1,4-Dichloro-5-hydroxy-9,10-anthracenedione (I) is alkylated with powdered potassium carbonate and benzyl bromide to give the ether (II). The ether is condensed with threee equivalents of 2-[(2-hydrazinoethyl)amino]ethanol in anhydrous dimethylsulfoxide to give regioisomers (III) and (IV), which are separated by flash silica gel chromatography. The isomer (III) is reacted with an excess of 2-[(2-aminoethyl)amino]ethanol in refluxing pyridine to give the intermediate (V). The intermediate is converted to the 10-hydroxy isomer by hydrogenolysis of the benzyl protecting group with Pearlman's catalyst in glacial acetic acid, followed by dihydrochloride salt formation.
Treatment of 1,4-dichloro-5,8-dihydroxy-9,10-anthracenedione (I) with K2CO3 and benzyl bromide gives the benzyl ether (II) in refluxing acetone, which, followed by treatment with 2-[(2-hydrazinoethyl)amino]ethanol in anhydrous Me2SO, gives product (III). Treatment of product (III) with excess [(2-aminoethyl)amino]methane in refluxing pyridine gives the 玹wo armed?compound, which, followed by treatment with Pearlman's catalyst in glacial AcOH, gives the target compound CI-937.